Triacetoxyperiodinane → tert-butyl (4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxobutyl)carbamate

HRID 459622Notes

Reaction equation

HRID 459622 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][C@H:24]([C:35]([NH:37][C:38]1[CH:39]=[N:40][N:41]([CH3:63])[C:42]=1[NH:43][C:44]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:36])[CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31]>C(Cl)Cl>[CH3:63][N:41]1[C:42]([NH:43][C:44]([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[C:38]([NH:37][C:35](=[O:36])[C:24](=[O:23])[CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH:39]=[N:40]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 69777655tert-butyl ((3S)-3-hydroxy-4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-4-oxobutyl)carbamate

Product 1

HCID 86597878tert-butyl (4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxobutyl)carbamateYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (4.2 g) was dissolved in methylene chloride (75 ml), and tert-butyl ((3S)-3-hydroxy-4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-4-oxobutyl)carbamate (5 g) was added to the solution. The whole mixture was stirred at room temperature for 30 minutes and quenched with 1N aqueous sodium hydroxide solution (70 ml) with stirring for 30 minutes. The whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product, which was purified by column chromatography on silica gel (ethyl acetate:methylene chloride=1:4) to give tert-butyl (4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxobutyl)carbamate (3.4 g).

Workup

  1. customquenched with 1N aqueous sodium hydroxide solution (70 ml)
  2. stirringwith stirring for 30 minutes
  3. extractionThe whole mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customto give a crude product, which
  8. customwas purified by column chromatography on silica gel (ethyl acetate:methylene chloride=1:4)

Sources & evidence

ORD record
ord-f85b39959022475ba04b5ed2038ca05a
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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